2-Acetamidothiazole → 2-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-fluoro-benzene propanamide

HRID 1982605Notes

Reaction equation

HRID 1982605 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:9])[CH3:8].[Cl:10][CH:11]([C:13]1[O:18][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:15]=2[N:14]=1)[CH3:12]>O1CCCC1.C([Li])CCC.CCCCCC>[Cl:10][CH:11]([CH3:12])[C:13]([NH:14][C:15]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](=[O:19])[CH2:8][C:7]([NH:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[O:9])=[O:18]

Participants

5

Reactant 2

HCID 176252-AcetamidothiazoleHCID 201456912-(1-Chloroethyl)-8-fluoro-4H-3,1-benzoxazin-4-one

Product 1

HCID 134230862-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-thiazolyl)-3-fluoro-benzene propanamideYield 39.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418244HCID 178418244, compoundSolvent

Procedure

Using the procedure of Step A of Example 6, a solution of 17 g of N-(2-thiazolyl)-acetamide in 340 ml of tetrahydrofuran, 160 ml of butyllithium-hexane solution and 0.06 moles of the product of Step D in 130 ml of tetrahydrofuran were reacted to obtain 8.7 g of 2-[(2-chloro-1-oxo-propyl)-amino]-β-oxo-N-(2-thiazolyl)-3-fluoro-benzene propanamide melting towards 170° C.

Sources & evidence

ORD record
ord-d97f7e7df5ad4573ab57dd2eed6f8765
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

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